Solid Phase Library Synthesis of Cyclic Depsipeptides:  Aurilide and Aurilide Analogues

Takahashi, Takashi; Nagamiya, Hiroyuki; Doi, Takayuki; Griffiths, Peter G.; Bray, Andrew M.

doi:10.1021/cc020091r

Cited by 47 publications

(21 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, aurilide B showed net tumor cell killing activity in the hollow fiber assay. There are currently two reports on the synthesis of aurilide analogues for SAR studies (Takahashi et al, 2003;Suenaga et al 2008). A structurally related compound, palau'amide (81) (Fig.…”

Section: Aurilides and Analoguesmentioning

confidence: 99%

Filamentous tropical marine cyanobacteria: a rich source of natural products for anticancer drug discovery

2010

View full text Add to dashboard Cite

show abstract

Section: Aurilides and Analoguesmentioning

confidence: 99%

Filamentous tropical marine cyanobacteria: a rich source of natural products for anticancer drug discovery

2010

View full text Add to dashboard Cite

show abstract

“…Aurilide showed unusually high in vivo antitumor activity in the NCI's hollow-fiber assays, and is expected to be a promising candidate for cancer treatment. Solid-phase library synthesis of aurilide and its derivatives was reported in 2003 [144]. Further structure-cytotoxicity relationship studies revealed that 6-epi-aurilide was almost non-cytotoxic (IC 50 > 4 µg/mL against HeLa S3 cells) [145].…”

Section: Peptides and Depsipeptidesmentioning

confidence: 99%

Antitumor Effects of Sea Hare-Derived Compounds in Cancer

Kigoshi

Kita

2014

Handbook of Anticancer Drugs From Marine Origin

View full text Add to dashboard Cite

Sea hares (family Aplysiidae) are a rich source of bioactive substances. Especially, over the past 40 years, the genera Aplysia and Dolabella have afforded numerous bioactive secondary metabolites that exhibit antitumor activity. For example, the depsipeptide dolastatin 10 and its analogue are currently in cancer clinical trials. Meanwhile, the chemical probe approach has revealed that the antitumor macrolide aplyronine A inhibits microtubule assembly in association with actin. This article highlights the recent findings regarding the chemical biology of antitumor and antineoplastic compounds from sea hares, as well as molecules that have been discovered and characterized after 2000.Keywords Antitumor · Sea hare · Aplysia · Antitumor · Actin-deplymerization · Cytotoxicity · Tubulin IntroductionSea hares, which belong to the opisthobranch group of mollusks (clade Aplysiomorpha), are shell-less, slow-moving benthic marine mollusks [1]. The order Anaspidea includes two families, Akeridae and Aplysiidae [2]. Almost all chemical studies have focused on Aplysiidae specimens. The family Aplysiidae includes nine genera, Aplysia (Linnaeus 1767), Bursatella (Blainville 1817), Dolabella (Lamarck 1801), Dolabrifera (Gray 1847), Notarchus (Cuvier 1817), Petalifera (Gray 1847), Phyllaplysia (Fischer 1872), Syphonota (Adams 1854), and Stylocheilus (Gould 1852). Sea hares are herbivorous, and are typically found on seaweed in shallow water. They are not eaten by other marine animals and have been postulated to contain chemical defense substances. The poisonous properties of sea hare secretions were known in Roman times. In addition, sea hares release ink from their ink glands, which deter predators. This ink acts as a screen, while at the

show abstract

“…Furthermore, the anti-proliferative effect of this molecule is suggested to operate via the mitochondrial mediated apoptosis based on studies using HCT8 and MCF7 cell lines. There is currently growing interest in developing aurilide-class of molecules as potential anticancer agents as indicated by several reports on its total syntheses and SAR studies [58][59][60][61].…”

Section: Aurilides/lagunamidesmentioning

confidence: 99%

Molecular Targets of Anticancer Agents from Filamentous Marine Cyanobacteria

Tan

Gupta

2014

Handbook of Anticancer Drugs From Marine Origin

View full text Add to dashboard Cite

The prokaryotic marine cyanobacteria, especially the filamentous forms, are known to produce a plethora of structurally unique natural products. A majority of these molecules are nitrogen-containing, belonging to the hybrid polyketide-polypeptide structural class. Various activities of clinical significance have been attributed to these molecules, ranging from anticancer, neuromodulating to antiprotozoal properties. Particularly in the area of cancer therapy, a number of potent marine cyanobacterial compounds, including dolastatins 10, 15, and largazole, have been identified as anticancer drug leads and are being further developed synthetically for clinical usage. The high potencies of these compounds are due to their exquisite interactions or interference with cellular pathways, specific macromolecules, or enzymes, such as the JAK-STAT signaling pathway, histone deacetylase, proteasome, protein kinase C, actin and microtubule filaments. This mini review covers more than 90 references and features more than 40 anticancer compounds, consisting of marine cyanobacterial natural products and their synthetic analogues. Biological data of these compounds are discussed based on their molecular targets.

show abstract

Solid Phase Library Synthesis of Cyclic Depsipeptides: Aurilide and Aurilide Analogues

Cited by 47 publications

References 23 publications

Filamentous tropical marine cyanobacteria: a rich source of natural products for anticancer drug discovery

Filamentous tropical marine cyanobacteria: a rich source of natural products for anticancer drug discovery

Antitumor Effects of Sea Hare-Derived Compounds in Cancer

Molecular Targets of Anticancer Agents from Filamentous Marine Cyanobacteria

Contact Info

Product

Resources

About